Episode Details

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Some bad dates are just awkward. Others turn into lifelong stories you tell when you need a reminder that you survived.

We’re Joe Flush and Eddie Penn, and we’re digging into the dating disasters that shaped us, from painfully quiet prom nights and getting stood up at a church hayride to the kind of confidence swings that make you kiss a screen door and still keep trying. We talk about how early rejection can harden into self-doubt, how that mindset can push people into the wrong relationships, and why learning to laugh at yourself is sometimes the first real step toward growth.

Then the stories get bigger: a dinner date derailed by nonstop sneezing, an attempted romantic parking spot interrupted by a cop, and online dating chaos before apps made it “easy.” There’s a declined credit card moment, a meal that suddenly costs more than planned, and a reminder that money stress and pride can wreck connection fast. We also touch marriage and divorce, the danger of living by a relationship script, and what it means to rebuild boundaries after everything falls apart.

By the end, we land somewhere surprisingly hopeful: being single can be fun, and the best dating lesson might be realizing you can make yourself whole again. If you’ve ever searched for bad date stories, online dating disasters, or honest relationship advice, you’ll feel seen here.

Listen now, subscribe, and if you laughed or winced, share it and leave a review. What’s the worst date you’ve ever had, and what did it teach you?

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Joe and Ed